DE555966C - Process for the preparation of acidic wool dyes of the anthraquinone series - Google Patents

Process for the preparation of acidic wool dyes of the anthraquinone series

Info

Publication number
DE555966C
DE555966C DE1930555966D DE555966DA DE555966C DE 555966 C DE555966 C DE 555966C DE 1930555966 D DE1930555966 D DE 1930555966D DE 555966D A DE555966D A DE 555966DA DE 555966 C DE555966 C DE 555966C
Authority
DE
Germany
Prior art keywords
weight
parts
preparation
anthraquinone series
wool dyes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE1930555966D
Other languages
German (de)
Inventor
Dr Ernst Diefenbach
Dr Georg Kraenzlein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Application granted granted Critical
Publication of DE555966C publication Critical patent/DE555966C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)

Description

DEUTSCHES REICHGERMAN EMPIRE

AUSGEGEBEN AM
4. AUGUST 1932ISSUED ON
AUGUST 4, 1932

REICHSPATENTAMTREICH PATENT OFFICE

PATENTSCHRIFTPATENT LETTERING

KLASSE 22 b GRUPPECLASS 22 b GROUP

I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M.*)I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M. *)

Zusatz zum Patent 554Addendum to Patent 554

Patentiert im Deutschen Reiche vom 18. Oktober 1930 ab Das Hauptpatent hat angefangen am 5. April 1930.Patented in the German Empire on October 18, 1930 The main patent started on April 5, 1930.

Im Hauptpatent 554 324 ist ein Verfahren zur Darstellung saurer Wollfarbstofre der Anthrachinonreihe beschrieben, welches darin besteht, daß man die Kondensationsprodukte aus ι-Amino- 4 - halogenanthrachinon-2-sulfosäuren und aromatischen Aminomono- oder -polycarbonsäuren in ihre Carbonsäureester überführt.In the main patent 554 324 a method for the preparation of acidic Wollfarbstofre is the Anthraquinone series described, which consists in the fact that the condensation products from ι-amino- 4 - halogenanthraquinone-2-sulfonic acids and aromatic amino mono- or polycarboxylic acids converted into their carboxylic acid esters.

Bei der weiteren Bearbeitung dieses Verfahr ens wurde nun gefunden, daß sich diese Farbstoffe auch in einer Operation durch direkte Kondensation der 1-Amino-4-halogenanthrachinon-2-sulfosäuren mit den Estern der aromatischen Aminomono- oder -polycarbonsäuren gewinnen lassen.In the further processing of this process it has now been found that this Dyes also in one operation through direct condensation of 1-amino-4-halogenanthraquinone-2-sulfonic acids can be obtained with the esters of the aromatic amino mono- or polycarboxylic acids.

BeispieleExamples

i. 40 Gewichtsteile 1 -amino-4-bromanthrachinon-2-sulfosaures Natrium, 16 Gewichtsteile Soda, 30 Gewichtsteile o-Aminobenzoesäureäthylester und 2 Gewichtsteile Rupferchlorür werden in 600 Gewichtsteilen Wasser 20 Stunden unter Rühren auf 90 bis 950 ervvärmt. Das Reaktionsgemisch wird zur Ab-Scheidung des Farbstoffes nach dem Erkalten mit Kochsalz versetzt, der Niederschlag abgesaugt und mit ioo/oiger Kochsalzlösung gut ausgewaschen. Zur weiteren Reinigung wird das Produkt in verdünnter Sodalösung gelöst und nach dem Filtrieren der Lösung durch Ansäuern mit Salzsäure oder durch Aussalzen gefällt.i. 40 parts by weight of sodium 1-amino-4-bromoanthraquinone-2-sulphonic acid, 16 parts by weight of soda, 30 parts by weight of ethyl o-aminobenzoate and 2 parts by weight of Rupferchlorur are heated in 600 parts by weight of water to 90 to 95 0 for 20 hours with stirring. In order to separate the dye, the reaction mixture is mixed with common salt after cooling, the precipitate is filtered off with suction and washed well with 100% common salt solution. For further purification, the product is dissolved in dilute soda solution and, after filtering the solution, precipitated by acidification with hydrochloric acid or by salting out.

2. 15 Gewichtsteile i-amino-4-bromanthrachinon - 2 - sulf osaures Natrium, 8 Gewichtsteile Natriumbicarbonat und 0,5 Gewichtsteile Kupferchlorid werden mit 400 Gewichtsteilen Wasser vermischt und auf 900 erwärmt. Zu dieser Mischung wird eine warme Lösung von ι s Gewichtsteilen o-Aminobenzyl-o-benzoesäureäthylester (erhalten aus der im Patent 553 001, Beispiel 1, beschriebenen 2'-Aminodiphenylmethan-2-carbonsäure durch. Behandeln mit Salzsäure und Äthylalkohol) in 50 Gewichtsteilen Pyridin hinzugefügt und das Gemisch 40 Stunden unter Rühren auf 90 bis 95° erwärmt. Aus der ReaktionsfLüssigkeit wird das Pyridin durch Dampfdestillation entfernt und der gebildete Farbstoff in üblicher Weise isoliert.2. 15 parts by weight of i-amino-4-bromoanthraquinone - 2 - sulf osaures sodium, 8 parts by weight of sodium bicarbonate and 0.5 parts by weight of copper chloride are mixed with 400 parts by weight of water and heated to 90 0th A warm solution of 50 parts by weight of o-aminobenzyl-o-benzoic acid ethyl ester (obtained from the 2'-aminodiphenylmethane-2-carboxylic acid described in Patent 553 001, Example 1 by treating with hydrochloric acid and ethyl alcohol) in 50 parts by weight is added to this mixture Pyridine was added and the mixture was heated to 90 to 95 ° for 40 hours while stirring. The pyridine is removed from the reaction liquid by steam distillation and the dye formed is isolated in the usual way.

3. 80 Gewichtsteile 1-amino-4-bromanthrachinon-2-sulfosaures Natrium, 40 Gewichtsteile Natriumbicarbonat und 3 Gewientsteile Kupferchlorür werden in 900 Gewichtsteile Wasser gegeben und mit einer Lösung von 50 Gewichtsteilen m-Aminobenzoesäureäthylester in 100 Gewichtsteilen Äthylalkohol ver-3. 80 parts by weight of 1-amino-4-bromoanthraquinone-2-sulfosaures Sodium, 40 parts by weight sodium bicarbonate and 3 parts by weight Copper chloride are added to 900 parts by weight of water and a solution of 50 parts by weight of ethyl m-aminobenzoate in 100 parts by weight of ethyl alcohol

*) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:

Dr. Georg Kränslein und Dr. Ernst Diefenbach in Frankfurt a. M.-Höchst.Dr. Georg Kränslein and Dr. Ernst Diefenbach in Frankfurt a. M.-Höchst.

setzt. Die Mischung wird unter Rühren io Stunden in mäßigem Sieden gehalten, dann zur Entfernung des Alkohols mit Dampf destilliert und der gebildete Farbstoff durch Aussalzen mit 300/oiger Kaliumchloridlösung isoliert.puts. The mixture is kept at a moderate boil for 10 hours while stirring, then distilled to remove the alcohol with steam and the dye formed through Salting out with 300% potassium chloride solution isolated.

4. 40 Gewichtsteile 1-amino-4-bromanthrachinon-2-sulfosaures Natrium, 20 Gewichtsteile Natriumcarbonat, gelöst in 600 Gewichts- teilen Wasser, werden mit einer Lösung von 25 Gewichtsteilen Aminoterephthalsäuredimethylester in 250 Gewichtsteilen Methylalkohol und 2 Gewichtsteilen Kupferchlorür versetzt. Die Mischung wird so lange bei 50 bis 6o° gerührt, bis die Farbstoffbildung beendet ist. Nachdem man den Alkohol mit Dampf abgetrieben hat, wird der Farbstoff in der üblichen Weise isoliert. Man erhält so ein violettes Pulver, welches auf Wolle grünstichig blaue Färbungen liefert.4. 40 parts by weight of 1-amino-4-bromoanthraquinone-2-sulfosaures Sodium, 20 parts by weight of sodium carbonate, dissolved in 600 parts by weight of water, with a solution of 25 parts by weight of dimethyl aminoterephthalate in 250 parts by weight of methyl alcohol and 2 parts by weight of copper chloride added. The mixture is stirred at 50 ° to 60 ° until the formation of the dye has ended is. After the alcohol has been driven off with steam, the dye is isolated in the usual manner. You get so a violet powder which produces greenish blue colorations on wool.

Claims (1)

Patentanspruch :Claim: Weitere Ausbildung des Verfahrens des Hauptpatents 554324 zur Darstellung von sauren Wollfarbstoffen der Anthrachinonreihe, dadurch gekennzeichnet, daß man hier 1 - Amino - 4 - halogenanthrachinon-2-sulfosäuren mit aromatischen Aminomono- oder -polycarbonsäureestem direkt kondensiert.Further development of the method of the main patent 554324 for the representation of acidic wool dyes of the anthraquinone series, characterized in that 1 - amino - 4 - halogenanthraquinone-2-sulfonic acids are used here directly condensed with aromatic amino mono- or polycarboxylic acid esters.
DE1930555966D 1930-04-04 1930-10-18 Process for the preparation of acidic wool dyes of the anthraquinone series Expired DE555966C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE541637T 1930-04-04
DE1930554324T DE554324C (en) 1930-04-04 1930-04-05 Process for the preparation of acidic wool dyes
DE555966T 1930-10-18
DE554325T 1930-12-25
DEI40422D DE587530C (en) 1930-04-04 1931-01-15 Process for the preparation of acidic dyes of the anthraquinone series

Publications (1)

Publication Number Publication Date
DE555966C true DE555966C (en) 1932-08-04

Family

ID=40497654

Family Applications (5)

Application Number Title Priority Date Filing Date
DE1930541637D Expired DE541637C (en) 1930-04-04 1930-04-04 Process for the preparation of anthraquinone derivatives
DE1930554324T Expired DE554324C (en) 1930-04-04 1930-04-05 Process for the preparation of acidic wool dyes
DE1930555966D Expired DE555966C (en) 1930-04-04 1930-10-18 Process for the preparation of acidic wool dyes of the anthraquinone series
DE1930554325D Expired DE554325C (en) 1930-04-04 1930-12-25 Process for the preparation of acidic wool dyes of the anthraquinone series
DEI40422D Expired DE587530C (en) 1930-04-04 1931-01-15 Process for the preparation of acidic dyes of the anthraquinone series

Family Applications Before (2)

Application Number Title Priority Date Filing Date
DE1930541637D Expired DE541637C (en) 1930-04-04 1930-04-04 Process for the preparation of anthraquinone derivatives
DE1930554324T Expired DE554324C (en) 1930-04-04 1930-04-05 Process for the preparation of acidic wool dyes

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE1930554325D Expired DE554325C (en) 1930-04-04 1930-12-25 Process for the preparation of acidic wool dyes of the anthraquinone series
DEI40422D Expired DE587530C (en) 1930-04-04 1931-01-15 Process for the preparation of acidic dyes of the anthraquinone series

Country Status (4)

Country Link
US (1) US1902084A (en)
DE (5) DE541637C (en)
FR (1) FR714775A (en)
GB (1) GB391262A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2453104A (en) * 1946-06-21 1948-11-02 Gen Aniline & Film Corp Aminoanthraquinone sulfonamides
US4267115A (en) * 1968-04-08 1981-05-12 Sandoz Ltd. Anthraquinone compounds
US4238400A (en) * 1978-07-07 1980-12-09 Imperial Chemical Industries Limited Anthraquinone dyes

Also Published As

Publication number Publication date
FR714775A (en) 1931-11-19
DE554324C (en) 1932-07-11
DE587530C (en) 1933-11-04
DE541637C (en) 1932-01-14
US1902084A (en) 1933-03-21
DE554325C (en) 1932-07-07
GB391262A (en) 1933-04-27

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